Multi-step reaction with 25 steps
1.1: 100 percent / NaBH4 / methanol
2.1: 85 percent / pyridine
3.1: 89 percent / K2CO3 / methanol
4.1: 84 percent / BF3*OEt2 / tetrahydrofuran / -78 °C
5.1: hydrochloric acid / tetrahydrofuran
5.2: 67 percent / TsOH / acetone
6.1: 97 percent / 4-(dimethylamino)pyridine; triethylamine
7.1: 83 percent / NaN3 / dimethylformamide / 120 °C
8.1: H2 / Pd/C
9.1: pyridine
10.1: n-butyllithium / tetrahydrofuran / -78 °C
10.2: tetrahydrofuran
11.1: 4-(dimethylamino)pyridine; triethylamine
12.1: Na(Hg) / methanol
13.1: 87 percent / pyridinium p-toluenesulfonate / methanol / 45 °C
14.1: 92 percent / imidazole
15.1: 100 percent / diisopropylethylamine
16.1: 100 percent / Bu4NF / tetrahydrofuran
17.1: 100 percent / NaBH4 / ethanol
18.1: 96 percent / ethyl acetate / Heating
19.1: Dess-Martin periodinane
20.1: NaClO2; resorcinol; NaH2PO4
21.1: 85 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride
22.1: 80 percent / NaHCO3 / acetonitrile
23.1: Bu4NF / tetrahydrofuran
24.1: trimethylphosphine / tetrahydrofuran
25.1: diphenylphosphoryl azide / dimethylformamide / 336 h
With
pyridine; 1H-imidazole; hydrogenchloride; dmap; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; n-butyllithium; sodium azide; sodium amalgam; boron trifluoride diethyl etherate; diphenylphosphoranyl azide; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; recorcinol; trimethylphosphane;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; ethanol; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;
19.1: Dess-Martin oxidation;
DOI:10.1002/anie.200352423